The 2026 Italian Open is the final big clay tournament ahead of the French Open.

There is a great semi-final match set between Jannik Sinner and Daniil Medvedev. The match begins at 1:00 p.m. ET on Friday, May 15.

Jannik Sinner vs. Daniil Medvedev Preview

There is no stopping Jannik Sinner at the moment. With his quarter-final victory over Alexander Rublev, Sinner broke Novak Djokovic’s record of 31 consecutive wins at ATP Masters 1000 events. He has won five consecutive Masters events and is two wins away from making this the sixth. Sinner is also playing some of the best tennis of his life heading into Roland-Garros, where Carlos Alcaraz will once again be absent. Sinner has seized on this moment with Alcaraz out with an injury and dominated his competition. At Roland-Garros, Sinner will get the chance to complete the Career Grand Slam just a few months after Alcaraz did it, keeping pace with his rival. A win here in Rome would also complete the Career Golden Masters for Sinner, something only Novak Djokovic has accomplished before.

Daniil Medvedev has what it takes to stop Jannik Sinner’s epic charge. Medvedev is one of the most volatile players in the game. However, he is also one of only a couple of players that has the raw talent to beat Jannik Sinner or Carlos Alcaraz on a big stage. Most players would need Sinner to give the match away to have a chance. If Medvedev is playing his best, he can go toe-to-toe with Sinner. The last 17 majors have been won by either Jannik Sinner, Carlos Alcaraz, Rafael Nadal or Novak Djokovic. The last player outside that group to win a major was Daniil Medvedev at the 2021 US Open.

Medvedev has shown flashes of being that guy again in 2026, just without the consistency. Medvedev won the Brisbane International to start the year and also won the title in Dubai. He also made it to the final at Indian Wells, where he lost to Sinner in a great match. Medvedev is once again showing his ceiling by making it to this semifinal. Medvedev won the title here in Rome in 2023. He is hoping to pull off this massive upset and get to the final once again.

Jannik Sinner vs. Daniil Medvedev Pick, Best Bet

Daniil Medvedev has always been a big-game hunter. When Novak Djokovic was the No. 1 player in the world, Daniil Medvedev beat him five times. Once Carlos Alcaraz became the No. 1 player in the world in 2023, he immediately beat Alcaraz in the US Open semi-finals. Medvedev also beat Jannik Sinner when he was World No. 1 at Wimbledon in 2024. Medvedev then recorded his eighth career win over the World No. 1 by beating Carlos Alcaraz at Indian Wells earlier this year. The Russian has a chance to take the top-ranked player in the world once again in Rome. A win over Sinner in this match would move Medvedev into a tie for 10th all-time in wins over No. 1-ranked players.

These two just met in a great final at Indian Wells. Sinner took care of business in two sets, but both sets went to a tiebreak. Medvedev was able to hang with Sinner every step of the way, but Sinner displayed his quality in those tiebreaks. I am backing Medvedev to be highly competitive against Sinner once again and cover this spread of +5.5 games. Medvedev struggles with his mental game and consistency on a tournament-by-tournament basis, but he is not afraid of the big moment. He will challenge Sinner and make him feel uncomfortable in a way that only two or three players in the world can. Sinner might edge him out in tiebreakers or win a set 7-5, but Medvedev should make this a highly competitive semi-final.

Best Bet: Daniil Medvedev +5.5 Games (-110)